TW434251B - Improved therapeutic agents - Google Patents

Improved therapeutic agents Download PDF

Info

Publication number: TW434251B
Authority: TW; Taiwan
Prior art keywords: ara; formula; derivative; hydrogen; treatment
Prior art date: 1995-07-25

Application number

TW085111996A

Other languages

English (en)

Chinese (zh)

Inventor

Finn Myhren

Bernt Borretzen

Are Dalen

Kjell Torgeir Stokke

Original Assignee

Norsk Hydro As

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1995-07-25

Filing date

1996-10-02

Publication date

2001-05-16

1996-10-02 Application filed by Norsk Hydro As filed Critical Norsk Hydro As

2001-05-16 Application granted granted Critical

2001-05-16 Publication of TW434251B publication Critical patent/TW434251B/zh

Links

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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/06—Pyrimidine radicals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/06—Antianaemics
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/052—Imidazole radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/056—Triazole or tetrazole radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/16—Purine radicals

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Molecular Biology (AREA)
Biotechnology (AREA)
Biochemistry (AREA)
Genetics & Genomics (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Medicinal Chemistry (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Hematology (AREA)
Oncology (AREA)
Bioinformatics & Cheminformatics (AREA)
Diabetes (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Artificial Filaments (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Polyamides (AREA)

TW085111996A 1995-07-25 1996-10-02 Improved therapeutic agents TW434251B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GBGB9515279.9A GB9515279D0 (en)	1995-07-25	1995-07-25	Improved therapeutic agents

Publications (1)

Publication Number	Publication Date
TW434251B true TW434251B (en)	2001-05-16

Family

ID=10778247

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
TW085111996A TW434251B (en)	1995-07-25	1996-10-02	Improved therapeutic agents

Country Status (25)

Country	Link
US (2)	US6316425B1 (de)
EP (1)	EP0842185B1 (de)
JP (2)	JP4372227B2 (de)
KR (1)	KR100401909B1 (de)
AT (1)	ATE207076T1 (de)
AU (1)	AU714814B2 (de)
CA (1)	CA2227533C (de)
CZ (1)	CZ291612B6 (de)
DE (1)	DE69616074T2 (de)
DK (1)	DK0842185T3 (de)
ES (1)	ES2166900T3 (de)
GB (1)	GB9515279D0 (de)
HU (1)	HU224839B1 (de)
IL (2)	IL122942A0 (de)
MX (1)	MX9800622A (de)
NO (1)	NO313985B1 (de)
NZ (1)	NZ313790A (de)
PL (1)	PL183601B1 (de)
PT (1)	PT842185E (de)
RU (1)	RU2165260C2 (de)
SK (1)	SK283003B6 (de)
TW (1)	TW434251B (de)
UA (1)	UA55389C2 (de)
WO (1)	WO1997005154A1 (de)
ZA (1)	ZA966047B (de)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6458772B1 (en)	1909-10-07	2002-10-01	Medivir Ab	Prodrugs
WO1998021223A1 (en) *	1996-11-12	1998-05-22	Medivir Ab	Nucleosides
ATE236188T1 (de) *	1997-01-24	2003-04-15	Conpharma As	Gemcitabin-derivate
RU2207573C2 (ru) *	2001-08-27	2003-06-27	Новичков Евгений Владимирович	Способ прогнозирования продолжительности жизни больных печеночно-клеточной карциномой
US7393862B2 (en) *	2002-05-17	2008-07-01	Celgene Corporation	Method using 3-(4-amino-1-oxo-1,3-dihydro-isoindol-2-yl)-piperidine-2,6-dione for treatment of certain leukemias
KR20060092242A (ko) *	2003-11-03	2006-08-22	코그니스 아이피 매니지먼트 게엠베하	아실 리보뉴클레오시드 및 아실 데옥시리보뉴클레오시드
NO324263B1 (no) *	2005-12-08	2007-09-17	Clavis Pharma Asa	Kjemiske forbindelser, anvendelse derav ved behandling av kreft, samt farmasoytiske preparater som omfatter slike forbindelser
US8497292B2 (en) *	2005-12-28	2013-07-30	Translational Therapeutics, Inc.	Translational dysfunction based therapeutics
EP2205073A4 (de) *	2007-09-26	2013-03-06	Sinai School Medicine	Azacytidin-analoge und ihre verwendungen
GB0808357D0 (en) *	2008-05-08	2008-06-18	Cyclacel Ltd	Process
KR20120086729A (ko) *	2009-11-20	2012-08-03	클라비스 파마 에이에스에이	젬시타빈 유도체의 비경구적 제제
RU2571283C2 (ru) *	2010-07-13	2015-12-20	Клавис Фарма Аса	Парентеральные составы производных элацитарабина
PL2832740T3 (pl) *	2012-03-28	2019-09-30	Fujifilm Corporation	Sól 1-(2-deoksy-2-fluoro-4-tio-beta-d-arabinofuranozylo)cytozyny
US12059427B2 (en)	2018-01-15	2024-08-13	Yinuoke Medicine Science And Technology Company Ltd.	Treatments for cachexia

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3894000A (en) *	1971-01-27	1975-07-08	Upjohn Co	Ara-cytidine derivatives and process of preparation
US4771056A (en) *	1985-08-29	1988-09-13	Roman Rozencwaig	Method of medical treatment with serotonin antagonists
CA2079413C (en)	1991-09-30	2003-09-09	Masakatsu Kaneko	Pyrimidine nucleoside derivatives having anti-tumor activity, their preparation and use
GB2266525A (en) *	1992-03-17	1993-11-03	Merck & Co Inc	Substituted cephalosporin sulfone compositions useful in the treatment of leukemia
GB9307043D0 (en)	1993-04-05	1993-05-26	Norsk Hydro As	Chemical compounds
US5641758A (en)	1993-11-10	1997-06-24	Kluge; Michael	Cytarabine derivatives, the preparation and use thereof

1995
- 1995-07-25 GB GBGB9515279.9A patent/GB9515279D0/en active Pending
1996
- 1996-07-12 RU RU98103238/04A patent/RU2165260C2/ru not_active IP Right Cessation
- 1996-07-12 AT AT96926032T patent/ATE207076T1/de active
- 1996-07-12 PT PT96926032T patent/PT842185E/pt unknown
- 1996-07-12 AU AU66335/96A patent/AU714814B2/en not_active Ceased
- 1996-07-12 PL PL96324690A patent/PL183601B1/pl not_active IP Right Cessation
- 1996-07-12 ES ES96926032T patent/ES2166900T3/es not_active Expired - Lifetime
- 1996-07-12 WO PCT/NO1996/000179 patent/WO1997005154A1/en not_active Ceased
- 1996-07-12 US US08/983,483 patent/US6316425B1/en not_active Expired - Lifetime
- 1996-07-12 IL IL12294296A patent/IL122942A0/xx active IP Right Grant
- 1996-07-12 DE DE69616074T patent/DE69616074T2/de not_active Expired - Lifetime
- 1996-07-12 JP JP50750497A patent/JP4372227B2/ja not_active Expired - Fee Related
- 1996-07-12 HU HU9900924A patent/HU224839B1/hu not_active IP Right Cessation
- 1996-07-12 NZ NZ313790A patent/NZ313790A/xx not_active IP Right Cessation
- 1996-07-12 SK SK80-98A patent/SK283003B6/sk not_active IP Right Cessation
- 1996-07-12 CA CA002227533A patent/CA2227533C/en not_active Expired - Fee Related
- 1996-07-12 EP EP96926032A patent/EP0842185B1/de not_active Expired - Lifetime
- 1996-07-12 CZ CZ1998163A patent/CZ291612B6/cs not_active IP Right Cessation
- 1996-07-12 KR KR10-1998-0700463A patent/KR100401909B1/ko not_active Expired - Fee Related
- 1996-07-12 DK DK96926032T patent/DK0842185T3/da active
- 1996-07-16 ZA ZA9606047A patent/ZA966047B/xx unknown
- 1996-10-02 TW TW085111996A patent/TW434251B/zh not_active IP Right Cessation
- 1996-12-07 UA UA98020922A patent/UA55389C2/uk unknown
1998
- 1998-01-15 IL IL122942A patent/IL122942A/en not_active IP Right Cessation
- 1998-01-21 MX MX9800622A patent/MX9800622A/es not_active IP Right Cessation
- 1998-01-23 NO NO19980296A patent/NO313985B1/no not_active IP Right Cessation
1999
- 1999-11-09 US US09/435,641 patent/US6335322B1/en not_active Expired - Fee Related
2009
- 2009-07-03 JP JP2009159081A patent/JP5087052B2/ja not_active Expired - Lifetime

Also Published As

Publication number	Publication date
CZ16398A3 (cs)	1998-06-17
NO980296L (no)	1998-01-23
ES2166900T3 (es)	2002-05-01
ZA966047B (en)	1997-02-04
DE69616074D1 (de)	2001-11-22
HUP9900924A2 (hu)	2001-05-28
CZ291612B6 (cs)	2003-04-16
ATE207076T1 (de)	2001-11-15
JP2009215326A (ja)	2009-09-24
HUP9900924A3 (en)	2001-06-28
RU2165260C2 (ru)	2001-04-20
NO313985B1 (no)	2003-01-13
JP5087052B2 (ja)	2012-11-28
WO1997005154A1 (en)	1997-02-13
CA2227533A1 (en)	1997-02-13
EP0842185A1 (de)	1998-05-20
JP2002504068A (ja)	2002-02-05
NO980296D0 (no)	1998-01-23
GB9515279D0 (en)	1995-09-20
KR100401909B1 (ko)	2004-02-14
PT842185E (pt)	2002-04-29
AU6633596A (en)	1997-02-26
IL122942A0 (en)	1999-05-09
JP4372227B2 (ja)	2009-11-25
US6316425B1 (en)	2001-11-13
SK283003B6 (sk)	2003-01-09
CA2227533C (en)	2007-01-09
UA55389C2 (uk)	2003-04-15
EP0842185B1 (de)	2001-10-17
MX9800622A (es)	1998-11-30
KR19990035804A (ko)	1999-05-25
PL324690A1 (en)	1998-06-08
NZ313790A (en)	1999-07-29
PL183601B1 (pl)	2002-06-28
SK8098A3 (en)	1998-07-08
DK0842185T3 (da)	2002-02-04
IL122942A (en)	2006-12-10
DE69616074T2 (de)	2002-06-06
US6335322B1 (en)	2002-01-01
AU714814B2 (en)	2000-01-13
HU224839B1 (en)	2006-03-28

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